Cyclopropylamine → 2-tert-Butyl-N-cyclopropyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonamide

HRID 1435415Notes

Reaction equation

HRID 1435415 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH:25]1([NH2:28])[CH2:27][CH2:26]1>CN(C1C=CN=CC=1)C.CC#N>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21]([NH:28][CH:25]3[CH2:27][CH2:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 236593032-tert-Butyl-N-cyclopropyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (76 mg, 0.20 mmol), cyclopropylamine (35 uL, 29 mg, 0.50 mmol) and DMAP (82 mg, 0.67 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 34 mg (43% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 0.45-0.51 (m, 2 H), 0.51-0.58 (m, 2 H), 1.49-1.65 (m, 4 H), 1.68 (s, 9 H), 2.10-2.22 (m, 1 H), 2.30-2.45 (m, 1 H), 3.31-3.41 (m, 2 H), 3.89-3.99 (m, 2 H), 4.54 (d, J=7.62 Hz, 2 H), 7.99 (dd, J=8.8, 1.8 Hz, 1 H), 8.07 (d, J=8.8 Hz, 1 H), 8.24 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=392.0; Anal. Calcd for C20H29N3O3S+1.30 TFA+0.40 EtOAc+0.5H2O (584.02): C, 49.77; H, 5.95; N, 7.20. Found: C, 49.78; H, 5.86; N, 7.20.

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-49a3fa2b05aa4b769cda6a3117aa927d
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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